2-Aminobiphenyl → ethyl N-biphenyl-2-yloxamate

HRID 2382154Notes

Reaction equation

HRID 2382154 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.Cl[C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(OCC)(=O)C>[C:3]1([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 70152-AminobiphenylHCID 8471TriethylamineHCID 20884Ethoxalyl chloride

Product 1

HCID 311876ethyl N-biphenyl-2-yloxamateYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

5.08 g (30 mmol) of 2-aminobiphenyl, 50 ml of ethyl acetate, and 3.1 g (30 mmol) of triethylamine were placed in a flask, to which 4.1 g (30 mmol) of ethyl chloroglyoxylate was added dropwise under ice cooling. The reaction mixture was stirred at room temperature for three hours, and then 50 ml of ethyl acetate was added thereto. The organic layer was washed with 30 ml of 1N hydrochloric acid and 30 ml of brine one by one, and then was dried with anhydrous sodium sulfate. The solvent was removed by evaporation to obtain 6.8 g (24 mmol, yield 85%) of ethyl N-biphenyl-2-yloxamate as colorless crystals.

Workup

  1. additionwas added dropwise under ice cooling
  2. washThe organic layer was washed with 30 ml of 1N hydrochloric acid and 30 ml of brine one by one
  3. dry with materialwas dried with anhydrous sodium sulfate
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-c50bfdd9cd174583b5a5e42ddf0d3cee
Source dataset
uspto-grants-2012_09
Patent number
US08258302B2

Reaction notes

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